Most traditional property managers don’t handle this setup due to challenges like managing tenant disputes, coordinating overlapping move-ins/outs, and the risk of Fair Housing violations when selecting tenants.

You mentioned the risk of an unsuccessful flip.

It depends on the property because each has its own risks.

Personal Circumstances: Consider your comfort level with debt and risk.

How much upfront costs are typically involved in a project before you know if it's a viable project to pursue? 

This was my first deal, and house hacking made the most sense because it lowered the threshold for risk in my mind.

I also am very interested in purchasing more STRs, and this is a really low risk way to see if I'm up for it (we have a 2.9% interest rate on our mortgage).My biggest concern is an ongoing plumbing issue we have had.

A single is find if it means less risk. 

Which level program were you involved in?

If they’re late a third time, you have a strong case for eviction for habitual non-payment—without risking the tenant showing up at the 11th hour with the money.For your specific circumstances, with only a partial month behind, I would guess there is a decent chance they can come even on rent and it would be a waste of your time.